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Record Information |
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Version | 4.0 |
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Status | Detected and Quantified |
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Creation Date | 2006-05-18 08:36:36 UTC |
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Update Date | 2020-11-09 23:16:14 UTC |
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HMDB ID | HMDB0001925 |
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Secondary Accession Numbers | - HMDB0001872
- HMDB01872
- HMDB01925
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Metabolite Identification |
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Common Name | Ibuprofen |
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Description | Ibuprofen is a nonsteroidal anti-inflammatory drug (NSAID) widely marketed under various trademarks including Act-3, Advil, Brufen, Motrin, Nuprin, and Nurofen. It is used for relief of symptoms of arthritis, primary dysmenorrhoea, and fever; Ibuprofen is an NSAID which is believed to work through inhibition of cyclooxygenase (COX), thus inhibiting prostaglandin synthesis. There are at least 2 variations of cyclooxygenase (COX-1 and COX-2), ibuprofen inhibits both COX-1 and COX-2. It appears that its analgesic, antipyretic, and anti-inflammatory activity are achieved principally through COX-2 inhibition; whereas COX-1 inhibition is responsible for its unwanted effects on platelet aggregation and the GI mucosa. As with other NSAIDs, ibuprofen inhibits platelet aggregation, but is not used therapeutically for this action since it is a minor and reversible effect. -- Wikipedia . |
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Structure | |
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Synonyms | Value | Source |
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(+-)-2-(p-Isobutylphenyl)propionic acid | ChEBI | (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid | ChEBI | (+-)-Ibuprofen | ChEBI | (+-)-p-Isobutylhydratropic acid | ChEBI | (4-Isobutylphenyl)-alpha-methylacetic acid | ChEBI | (RS)-Ibuprofen | ChEBI | 2-(4-Isobutylphenyl)propanoic acid | ChEBI | 4-Isobutylhydratropic acid | ChEBI | Adran | ChEBI | Advil | ChEBI | alpha-(4-Isobutylphenyl)propionic acid | ChEBI | alpha-(p-Isobutylphenyl)propionic acid | ChEBI | Amibufen | ChEBI | Anco | ChEBI | Anflagen | ChEBI | Apsifen | ChEBI | Bluton | ChEBI | Brufen | ChEBI | Brufort | ChEBI | Buburone | ChEBI | Butylenin | ChEBI | Dolgin | ChEBI | Dolgirid | ChEBI | Dolgit | ChEBI | Dolo-dolgit | ChEBI | Ebufac | ChEBI | Epobron | ChEBI | Femadon | ChEBI | Haltran | ChEBI | Ibu-attritin | ChEBI | Ibumetin | ChEBI | Ibuprocin | ChEBI | Ibutid | ChEBI | Inabrin | ChEBI | Inoven | ChEBI | Lamidon | ChEBI | Lebrufen | ChEBI | Liptan | ChEBI | Medipren | ChEBI | Motrin | ChEBI | Mynosedin | ChEBI | Nobfen | ChEBI | Nobgen | ChEBI | Nuprin | ChEBI | Nurofen | ChEBI | Pediaprofen | ChEBI | Roidenin | ChEBI | Rufen | ChEBI | Seclodin | ChEBI | Suspren | ChEBI | Tabalon | ChEBI | Trendar | ChEBI | Urem | ChEBI | (+-)-2-(p-Isobutylphenyl)propionate | Generator | (+-)-a-Methyl-4-(2-methylpropyl)benzeneacetate | Generator | (+-)-a-Methyl-4-(2-methylpropyl)benzeneacetic acid | Generator | (+-)-alpha-Methyl-4-(2-methylpropyl)benzeneacetate | Generator | (+-)-Α-methyl-4-(2-methylpropyl)benzeneacetate | Generator | (+-)-Α-methyl-4-(2-methylpropyl)benzeneacetic acid | Generator | (+-)-p-Isobutylhydratropate | Generator | (4-Isobutylphenyl)-a-methylacetate | Generator | (4-Isobutylphenyl)-a-methylacetic acid | Generator | (4-Isobutylphenyl)-alpha-methylacetate | Generator | (4-Isobutylphenyl)-α-methylacetate | Generator | (4-Isobutylphenyl)-α-methylacetic acid | Generator | 2-(4-Isobutylphenyl)propanoate | Generator | 4-Isobutylhydratropate | Generator | a-(4-Isobutylphenyl)propionate | Generator | a-(4-Isobutylphenyl)propionic acid | Generator | alpha-(4-Isobutylphenyl)propionate | Generator | Α-(4-isobutylphenyl)propionate | Generator | Α-(4-isobutylphenyl)propionic acid | Generator | a-(p-Isobutylphenyl)propionate | Generator | a-(p-Isobutylphenyl)propionic acid | Generator | alpha-(p-Isobutylphenyl)propionate | Generator | Α-(p-isobutylphenyl)propionate | Generator | Α-(p-isobutylphenyl)propionic acid | Generator | alpha-p-Isobutylphenylpropionate | HMDB | alpha-p-Isobutylphenylpropionic acid | HMDB | Duralbuprofen | HMDB | p-Isobutyl-2-phenylpropionate | HMDB | p-Isobutyl-2-phenylpropionic acid | HMDB | p-Isobutylhydratropate | HMDB | p-Isobutylhydratropic acid | HMDB | Calcium salt ibuprofen | HMDB | Ibuprofen, copper (2+) salt | HMDB | Ibuprofen, magnesium salt | HMDB | Ibuprofen, zinc salt | HMDB | Trauma dolgit gel | HMDB | Aluminum salt ibuprofen | HMDB | IP 82 | HMDB | Ibuprofen, aluminum salt | HMDB | Ibuprofen-zinc | HMDB | Magnesium salt ibuprofen | HMDB | Salt ibuprofen, magnesium | HMDB | Sodium salt ibuprofen | HMDB | Zinc salt ibuprofen | HMDB | I.V. solution, ibuprofen | HMDB | IP-82 | HMDB | Ibuprofen i.v. solution | HMDB | Ibuprofen, (+-)-isomer | HMDB | Ibuprofen, (R)-isomer | HMDB | Ibuprofen, (S)-isomer | HMDB | Ibuprofen, calcium salt | HMDB | Potassium salt ibuprofen | HMDB | Salprofen | HMDB | Salt ibuprofen, sodium | HMDB | Salt ibuprofen, zinc | HMDB | alpha-Methyl-4-(2-methylpropyl)benzeneacetic acid | HMDB | Ibuprofen zinc | HMDB | Ibuprofen, potassium salt | HMDB | Ibuprofen, sodium salt | HMDB | Trauma-dolgit gel | HMDB | TraumaDolgit gel | HMDB |
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Chemical Formula | C13H18O2 |
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Average Molecular Weight | 206.2808 |
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Monoisotopic Molecular Weight | 206.13067982 |
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IUPAC Name | 2-[4-(2-methylpropyl)phenyl]propanoic acid |
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Traditional Name | ibuprofen, (+-)- |
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CAS Registry Number | 15687-27-1 |
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SMILES | CC(C)CC1=CC=C(C=C1)C(C)C(O)=O |
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InChI Identifier | InChI=1S/C13H18O2/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15/h4-7,9-10H,8H2,1-3H3,(H,14,15) |
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InChI Key | HEFNNWSXXWATRW-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as phenylpropanoic acids. Phenylpropanoic acids are compounds with a structure containing a benzene ring conjugated to a propanoic acid. |
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Kingdom | Organic compounds |
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Super Class | Phenylpropanoids and polyketides |
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Class | Phenylpropanoic acids |
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Sub Class | Not Available |
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Direct Parent | Phenylpropanoic acids |
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Alternative Parents | |
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Substituents | - 2-phenylpropanoic-acid
- P-cymene
- Aromatic monoterpenoid
- Monocyclic monoterpenoid
- Monoterpenoid
- Phenylpropane
- Monocyclic benzene moiety
- Benzenoid
- Monocarboxylic acid or derivatives
- Carboxylic acid
- Carboxylic acid derivative
- Organooxygen compound
- Carbonyl group
- Organic oxygen compound
- Hydrocarbon derivative
- Organic oxide
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Health effect: |
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Disposition | Source: Route of exposure: Biological location: |
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Process | Naturally occurring process: |
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Role | Biological role: Environmental role: Industrial application: |
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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 76 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 0.021 mg/mL at 25 °C | Not Available | LogP | 3.97 | AVDEEF,A (1997) |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-02t9-1910000000-23f448d7be7d5cc35682 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-02t9-1910000000-cbe52d63986b68a2cec0 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (1 TMS) | splash10-00di-9300000000-cc259b7768023e4cdba8 | Spectrum | GC-MS | GC-MS Spectrum - EI-B (Non-derivatized) | splash10-03di-3910000000-618880f8fd7b8ec3d473 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-02t9-1910000000-23f448d7be7d5cc35682 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-02t9-1910000000-cbe52d63986b68a2cec0 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9300000000-cc259b7768023e4cdba8 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0296-3900000000-497aad6d6a3e7af1ac0a | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-0309-8940000000-13dc492b216fb21dde05 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-03di-0910000000-90bf6813134491c9fbfd | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-001i-9800000000-56f599abc462380b648c | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - EI-B (HITACHI RMU-6E) , Positive | splash10-03di-3910000000-618880f8fd7b8ec3d473 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0006-0497000000-fa397d6ffd29da116900 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-qTof , Positive | splash10-0a4i-0690000000-f598b8bee69a6b62e817 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-1900000000-f1b7a986fee133d97eb1 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - , positive | splash10-03di-0920000000-aa36b3244e32560bb9d5 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4i-1970000000-50ac0f9eaf22b22ff57f | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0bti-2910000000-a5804838ebd627fea205 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0pb9-4900000000-a5b30d0a96d30db5ea4a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-0490000000-27a27175d7bf2807ff33 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-08fr-1940000000-f33172b037148de8a091 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-02ha-5900000000-ebc408aaffe3ab58a6a3 | Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-03xr-3900000000-e20ef3c30496e17720ba | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | - Extracellular
- Membrane (predicted from logP)
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Biospecimen Locations | - Blood
- Cerebrospinal Fluid (CSF)
- Urine
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Tissue Locations | - Adipose Tissue
- Adrenal Cortex
- Adrenal Gland
- Bladder
- Epidermis
- Fibroblasts
- Intestine
- Kidney
- Neuron
- Pancreas
- Placenta
- Platelet
- Prostate
- Skeletal Muscle
- Spleen
- Testis
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Pathways | |
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Normal Concentrations |
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Blood | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details | Blood | Detected and Quantified | 242.0 (2.42-485.0) uM | Adult (>18 years old) | Both | Normal | | details | Urine | Detected and Quantified | 6.513 +/- 6.212 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Normal | | details | Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Cerebrospinal Fluid (CSF) | Detected and Quantified | 1.528 +/- 0.563 uM | Adult (>18 years old) | Both | nerve root compression pain | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.815 +/- 0.296 uM | Adult (>18 years old) | Both | nerve root compression pain | | details | Cerebrospinal Fluid (CSF) | Detected and Quantified | 0.000592 +/- 0.000170 uM | Adult (>18 years old) | Both | Bronchial carcinoma | | details | Urine | Detected and Quantified | 3.408 +/- 2.229 umol/mmol creatinine | Children (1 - 13 years old) | Not Specified | Eosinophilic esophagitis | | details |
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Predicted Concentrations |
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Blood | 0.000 umol/mmol creatinine | Adult (>18 years old) | Both | Normal | Predicted based on drug qualities |
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Associated Disorders and Diseases |
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Disease References | Eosinophilic esophagitis |
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- (). Mordechai, Hien, and David S. Wishart. .
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Associated OMIM IDs | - 610247 (Eosinophilic esophagitis)
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External Links |
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DrugBank ID | DB01050 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022743 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 3544 |
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KEGG Compound ID | C01588 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Ibuprofen |
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METLIN ID | 572 |
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PubChem Compound | 3672 |
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PDB ID | Not Available |
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ChEBI ID | 5855 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Perioli L, Ambrogi V, Angelici F, Ricci M, Giovagnoli S, Capuccella M, Rossi C: Development of mucoadhesive patches for buccal administration of ibuprofen. J Control Release. 2004 Sep 14;99(1):73-82. [PubMed:15342182 ]
- Whitlam JB, Brown KF, Crooks MJ, Room GF: Transsynovial distribution of ibuprofen in arthritic patients. Clin Pharmacol Ther. 1981 Apr;29(4):487-92. [PubMed:7471614 ]
- Al-Saidan SM: Transdermal self-permeation enhancement of ibuprofen. J Control Release. 2004 Nov 24;100(2):199-209. [PubMed:15544868 ]
- Albert KS, Gernaat CM: Pharmacokinetics of ibuprofen. Am J Med. 1984 Jul 13;77(1A):40-6. [PubMed:6465162 ]
- Alam I, Ferrell LD, Bass NM: Vanishing bile duct syndrome temporally associated with ibuprofen use. Am J Gastroenterol. 1996 Aug;91(8):1626-30. [PubMed:8759674 ]
- Townsend RJ, Benedetti TJ, Erickson SH, Cengiz C, Gillespie WR, Gschwend J, Albert KS: Excretion of ibuprofen into breast milk. Am J Obstet Gynecol. 1984 May 15;149(2):184-6. [PubMed:6720796 ]
- Horn AC, Jarrett SW: Ibuprofen-induced aseptic meningitis in rheumatoid arthritis. Ann Pharmacother. 1997 Sep;31(9):1009-11. [PubMed:9296242 ]
- Van Overmeire B, Allegaert K, Casaer A, Debauche C, Decaluwe W, Jespers A, Weyler J, Harrewijn I, Langhendries JP: Prophylactic ibuprofen in premature infants: a multicentre, randomised, double-blind, placebo-controlled trial. Lancet. 2004 Nov 27-Dec 3;364(9449):1945-9. [PubMed:15567010 ]
- Castillo M, Smith PC: Disposition and reactivity of ibuprofen and ibufenac acyl glucuronides in vivo in the rhesus monkey and in vitro with human serum albumin. Drug Metab Dispos. 1995 May;23(5):566-72. [PubMed:7587932 ]
- Hockertz S, Heckenberger R, Emmendorffer A, Muller M: Influence of ibuprofen on the infection with Listeria monocytogenes. Arzneimittelforschung. 1995 Jan;45(1):104-7. [PubMed:7893261 ]
- Day RO, Williams KM, Graham GG, Lee EJ, Knihinicki RD, Champion GD: Stereoselective disposition of ibuprofen enantiomers in synovial fluid. Clin Pharmacol Ther. 1988 May;43(5):480-7. [PubMed:3365913 ]
- Trappe TA, White F, Lambert CP, Cesar D, Hellerstein M, Evans WJ: Effect of ibuprofen and acetaminophen on postexercise muscle protein synthesis. Am J Physiol Endocrinol Metab. 2002 Mar;282(3):E551-6. [PubMed:11832356 ]
- Laffi G, Daskalopoulos G, Kronborg I, Hsueh W, Gentilini P, Zipser RD: Effects of sulindac and ibuprofen in patients with cirrhosis and ascites. An explanation for the renal-sparing effect of sulindac. Gastroenterology. 1986 Jan;90(1):182-7. [PubMed:3079594 ]
- Goldenberg NA, Jacobson L, Manco-Johnson MJ: Brief communication: duration of platelet dysfunction after a 7-day course of Ibuprofen. Ann Intern Med. 2005 Apr 5;142(7):506-9. [PubMed:15809462 ]
- Yao M, Zhou W, Sangha S, Albert A, Chang AJ, Liu TC, Wolfe MM: Effects of nonselective cyclooxygenase inhibition with low-dose ibuprofen on tumor growth, angiogenesis, metastasis, and survival in a mouse model of colorectal cancer. Clin Cancer Res. 2005 Feb 15;11(4):1618-28. [PubMed:15746067 ]
- Jabor VA, Lanchote VL, Bonato PS: Enantioselective analysis of ibuprofen in human plasma by anionic cyclodextrin-modified electrokinetic chromatography. Electrophoresis. 2002 Sep;23(17):3041-7. [PubMed:12207314 ]
- Salas-Herrera IG, Pearson RM, Turner P: Concentration of ibuprofen in cervical mucus. J Pharm Pharmacol. 1991 Feb;43(2):142-4. [PubMed:1672904 ]
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